How To Tell
by Where's Waldorf
Summary: Set after the GG identity reveal. Jenny and Nate's chance at figuring it out. "So you're a fan of the designer, huh?" Jenny asked boldly in a voice that wasn't her own. "Always have been," he replied quietly.
1. Chapter 1

**I know, I know. ****I'm in the middle of exams and I have no right to be writing. But this story is, as Jenny Humphrey said, "last minute inspiration." ****This was supposed to be a finished one shot but I realized that I want a space to release my Nenny feels. So I'm extending it into a story, but with quickly updated short chapters because it's already been half-written.**** It could get OOC and silly because I inject my own personality in it here and there. But I try to add in little tid-bits and feels that I get from Nenny and the show as a whole. **

* * *

It started off innocent.

He liked everything she would put on Facebook.

Maybe he just thought that her posts were funny, or he was genuinely interested in the different things she was doing in London.

Whatever it was, it didn't stop her from smiling at the screen every time she got the notification.

Jenny often wondered what passed through his mind when he read them, and was intrigued when he _didn't_ like the status: _"Day 3 of working with male models for swimsuit line."_

She posted things knowing that he would see them, and she unconsciously began to put genuine effort into making them perfect.

It eventually got to the point where it was late at night and she would post something between last minute designs before her deadline. Jenny wouldn't be able to do anything until he liked it. Like a drug addict she'd hold her breath until she could let out a sigh of relief when she saw the blessed red number.

That was the first sign of trouble.

Dan and Serena welcomed her back to their world via a dinner party less than a year after Dan was outed as Gossip Girl.

She had missed the city.

The space had been good for her. She had learnt so much in London from so many different people. But there was still that Jenny Humphrey energy that had carried with her all the way to adulthood. She had just learnt how to harness it now.

He greeted her with a welcoming hug.

"It's good to see you, Jen," Nate said when he pulled back.

And no new edge that she had developed over her time away could prevent her from getting that nervous fluttery feeling inside that she always got when he spoke to her.

At dinner he laughed loudly at everything she said, and she couldn't help but go silent and guarded at his complete attention.

It was foreign to her.

He asked her about fashion, and if she could offer an insight into it for him when it came to the fashion section of The Spectator.

They exchanged numbers.

It was interesting how their phone conversations were held at the dead of night, and that they talked about fashion for about half a minute before Nate completely changed the subject. Jenny ended up having bags under her eyes for work at Waldorf every morning after their night long conversations about everything under the sun.

But still, she wasn't about to complain.

They joked around the way they used to, and sometimes she could swear that he was flirting with her.

"Our first fashion show is in a matter of weeks. What if no one shows up?" Jenny said nervously one night.

"Of course they're going to show up. The designer alone is reason enough," he replied with a chuckle.

She was silent for a moment.

"So you're a fan of the designer, huh?" Jenny asked boldly in a voice that isn't her own.

"Always have been," he replied quietly.

She was breathless.


	2. Chapter 2

The thing about Jenny was that she wasn't a denier.

She was completely aware of the fact that every time their phone calls ended, she had a ridiculous grin on her face.

A lot like the grin a person got when they liked someone.

And then almost naturally the girly habits began to occur. The day dreaming, the fantasizing. She often realized with horror that she was doodling his name on her notepad at work. Hadn't she once said that she would never get to that point with a guy?

Then there was the heart-stopping moment when Blair had been flicking through her sketches and caught the N.A inside a detailed heart that she had spent an obscene amount of time on instead of her designs.

"It's a...symbol that we could try out," Jenny quickly covered.

"What does it stand for?" Blair asked.

Jenny stared at her with wide eyes as she scanned her brain for anything that made sense.

"Not...Angelic," Jenny said slowly.

Blair furrowed her eyebrows.

Jenny cursed herself. Her own ears didn't believe it, let alone Blair Waldorf's.

"I'll think about it, I guess," Blair said, tapping her pen as she stared at her contemplatively.

And now this crush of hers had caused her to be under her boss's suspicion.

Another sign of trouble.

* * *

One day, Nate randomly texted her at work just to send a meme about Twilight, and she laughed out loud, causing Blair to probe her with questions until she admitted that she had been speaking to Nate.

Blair looked impressed, and Jenny beamed inwardly. The desire to win Blair's respect never went away.

She put on an expression of dignified modesty instead, and played it off as nothing.

But Blair had this look on her face, a twisted pout of a smirk.

Jenny asked her what it was, and Blair went all high-pitched and doe eyed.

"Oh nothing," Blair said.

But before Jenny left that day, Blair invited her to have dinner at Gramercy Tavern.

Now, Jenny wasn't stupid. She had rallied against Blair enough times to know when she was up to something. But as always, she was willing to play her little game.

"What time?" Jenny said, flickering head as if to say, "let's see what you've got."

* * *

And so Jenny turned up to the restaurant, donning her own short and body-hugging black number.

The waiter showed her to the table, and when she saw who was seated on it, her heart jumped into her throat.

"Jenny?" He said, looking up at her with a surprised but pleased look.

"Nate," she said breathily.

Jenny was frozen on the spot. She couldn't move, she couldn't speak. All the heat rushed to her cheeks as her mind turned to mush. The fact that he was currently all Ralph Lauren and slicked back hair didn't help.

_Get it together Humphrey. He's just Nate. A really attractive, older Nate who you'd like to do._

She moved to sit down, and that's when she realized the table was just for two.

Damn, Blair was good.

As if on cue, both of their phones lit up with texts.

_'Sorry, couldn't find someone to look after Henry. Enjoy dinner!'_ Jenny read.

"Chuck cancelled on me," Nate said aloud, holding up his phone.

Jenny looked back up at him wordlessly, blinking for a moment.

"Well," he said with an awkward chuckle.

It was uncomfortable and tense, and Jenny found herself standing up before she could stop herself.

"I guess this will have to happen another time," she blurted quickly, overwhelmed by self-consciousness and embarrassment.

_What are you doing?_

"Right," Nate said quietly with this look on his face. Later, when she over-analysed it in her head from the comfort of her own shower, she realized that it may have been disappointment.

"See ya," Jenny said in a syrupy voice, knocking into a passing by waiter, before leaving the restaurant all together.

_You're an absolute idiot. _

For some reason, she had built up speaking to him in person after all those long, nightly phone calls to something out of a romantic comedy. She was going to charm him, and they were going to end up at his place. Then he was going to sweep her off her feet, literally and metaphorically.

In reality, when faced with him, it was an awkward, unanticipated mess.

She just couldn't deal.

And now there appeared to be no available taxis within the vicinity, making matters worse. She blinked back the tears of frustration that burned in her eyes.

_This night officially sucks_.

She pressed her lips together in an attempt to repress the building sob.

"Hey," she heard someone behind her say.

She turned around rapidly.

"Nate," Jenny said, hoping her voice didn't waver too obviously.

"Come on," he said quietly, placing his hand on the small of her back and leading her to his waiting town car.

There was always something warm about him doing that, whether it was rescuing her from being photographed in her underwear or putting her in a cab after a long night of talking about their complicated parents. It made her comply without a word.

They sat in silence once they got in the car, only speaking to confirm where she wanted to be dropped off.

"Dan's," she had said softly.

Jenny fiddled with her phone for a bit, distracting herself, before placing her hands on either side of her on the seat.

"Thanks," she managed to whisper after a long time.

"Don't mention it," he replied.

He was so close, the smallest of spaces between them. She could smell his aftershave, and it made her feel dizzy.

_Say something. Anything. _

But she couldn't speak. Her mind was a jumble. His presence was overwhelming her.

She felt a light, feather-like touch on her right hand, and she realized that it was his pinkie stroking the top of her palm. Her hand shook slightly as she moved it under his so he could thread his fingers between hers.

Jenny didn't dare look at him.

They reached Dan and the Van der Woodsen's building, and he released her hand reluctantly.

She escaped the car without glancing back, practically scrambling out.

Jenny didn't get a wink of sleep that night, lost in her own thoughts.

What had happened to her over the years?

She used to be ruthless in her want for him, and would have leaped at the opportunity she had been given tonight. But she didn't dare anything with him anymore, no matter how much she wanted to.

Jenny Humphrey had lost her guts when it came to Nate Archibald.

And you couldn't blame her. Whenever she had put herself out there in the past she had been pushed away by him. Even the most fearless of people had their limits, and she definitely had a problem with how far she took things. Her life had spiraled out of control fast when she became too desperate to have it all, almost losing those closest to her.

She had learned to hesitate.

But...was it different this time? Was _he_ different?

Jenny didn't know, and she also felt that it was going to be impossible to find out without putting herself out there.

But as Dan had once written, it was an open heart that was vulnerable to the deepest wound.

She wasn't sure that she was ready for that just yet.


End file.
